U.S. patent application number 10/333664 was filed with the patent office on 2003-09-11 for oxidation dyeing composition for keratinous fibres and dyeing method using same.
Invention is credited to Lang, Gerard.
Application Number | 20030167579 10/333664 |
Document ID | / |
Family ID | 8847772 |
Filed Date | 2003-09-11 |
United States Patent
Application |
20030167579 |
Kind Code |
A1 |
Lang, Gerard |
September 11, 2003 |
Oxidation dyeing composition for keratinous fibres and dyeing
method using same
Abstract
The invention concerns a ready-to-use oxidation dyeing
composition for keratinous fibres, and in particular human
keratinous fibres such as hair comprising, in a suitable dyeing
medium, at least an oxidation base selected among certain
substituted paraphenylenediamine derivatives and their addition
salts with an acid, at least an alkaline agent and hydrogen
peroxide, and the dyeing method using said composition.
Inventors: |
Lang, Gerard; (Saint Prix,
FR) |
Correspondence
Address: |
FINNEGAN, HENDERSON, FARABOW, GARRETT & DUNNER
LLP
1300 I STREET, NW
WASHINGTON
DC
20005
US
|
Family ID: |
8847772 |
Appl. No.: |
10/333664 |
Filed: |
April 10, 2003 |
PCT Filed: |
March 5, 2001 |
PCT NO: |
PCT/FR01/00646 |
Current U.S.
Class: |
8/405 ; 8/406;
8/408; 8/415; 8/421 |
Current CPC
Class: |
A61K 8/411 20130101;
A61K 8/4913 20130101; A61K 8/492 20130101; A61K 8/494 20130101;
A61K 8/4926 20130101; A61Q 5/10 20130101 |
Class at
Publication: |
8/405 ; 8/406;
8/408; 8/415; 8/421 |
International
Class: |
A61K 007/13 |
Foreign Application Data
Date |
Code |
Application Number |
Mar 6, 2000 |
FR |
00/02860 |
Claims
1. A ready-to-use composition for the oxidation dyeing of keratin
fibers, in particular of human keratin fibers such as the hair,
characterized in that it comprises, in a medium that is suitable
for dyeing: (A) at least one oxidation base chosen from the
substituted para-phenylenediamine derivatives of formula (I) below,
and the addition salts thereof with an acid: 3 in which: R.sub.1
and R.sub.2 can take one of the following meanings i) to v) below:
i) R.sub.1 and R.sub.2 simultaneously represent a
--(CH.sub.2).sub.2CHOHCH.sub.2OH radical; or ii) R.sub.1 represents
a --CH.sub.2(CHOH).sub.4CH.sub.2OH radical and R.sub.2 represents a
hydrogen atom, an alkyl or aryl radical or a heterocycle; or iii)
R.sub.1 represents an alkyl or aryl radical or a heterocycle and
R.sub.2 represents an alkylene radical --(CH.sub.2).sub.m-- in
which m is an integer equal to 2 or 3, said alkylene radical
forming a ring together with the nitrogen atom, the carbon atom of
the benzene ring bearing the nitrogen atom and one of the two
carbon atoms of the benzene ring that are adjacent to it, it being
understood that when R.sub.1 is an alkyl or aryl radical, then
either R.sub.1 or said alkylene radical is substituted with a
radical containing at least one nitrogen, oxygen or sulfur atom;
iv) R.sub.1 represents a radical --(CH.sub.2CH.sub.2O).sub.pR.sub.4
in which p is an integer between 2 and 8 inclusive, R.sub.4 and
R.sub.2, which may be identical or different, represent a hydrogen
atom, an alkyl or aryl radical or a heterocycle; v) R.sub.1 and
R.sub.2 form, together with the nitrogen atom to which they are
attached, a 5-, 6- or 7-membered saturated heterocycle, said
heterocycle being substituted with at least one radical containing
at least one carbon, nitrogen, oxygen or sulfur atom; R.sub.3
represents a halogen atom, an alkyl or aryl radical, a cyano,
nitro, hydroxyl, carboxyl, sulfo, alkoxy, aryloxy, cyanoamino,
amino, anilino, ureido, sulfamylamino, mono- or
dialkylsulfamylamino, alkylthio, arylthio, alkoxycarbonylamino,
sulfonamido, carbamyl, mono- or dialkylcarbamylsulfamyl, sulfonyl,
alkoxycarbonyl, azo, acyloxy, carbamyloxy, mono- or
dialkylcarbamyloxy, silyl, silyloxy, aryloxycarbonylamino, imido,
sulfinyl, phosphonyl, aryloxycarbonyl, acyl or mercapto radical, a
heterocycle or a heterocycle linked to the benzene ring of formula
(I) via an ether or thio bond; said alkyl radicals containing from
1 to 25 carbon atoms and possibly being linear, branched or cyclic
and possibly being substituted with one or more radicals, and in
this case possibly representing a mono- or polyhydroxyalkyl
radical, an alkoxyalkyl radical, an aminoalkyl radical optionally
substituted on the nitrogen atom, or a carboxyalkyl,
alkylcarboxyalkyl, thioalkyl, alkylthioalkyl, cyanoalkyl,
trifluoroalkyl, sulfoalkyl, phosphoalkyl or haloalkyl radical; said
alkoxy radicals containing from 1 to 25 carbon atoms and possibly
being linear, branched or cyclic; said aryl radicals containing
from 6 to 26 carbon atoms and possibly being substituted with one
or more radicals chosen from alkyl, substituted alkyl and alkoxy
radicals; the heterocycles being monocyclic or polycyclic, each
ring being 3-, 4-, 5- or 6-membered and possibly containing one or
more hetero atoms, it being understood that in the case of
polycyclic heterocycles, at least one of the rings contains at
least one hetero atom such as N, O or S; n is an integer between 0
and 4; it being understood that when n is greater than 1, then the
radicals R.sub.3 may be identical or different and may together
form a 3-, 4-, 5- or 6-membered saturated or unsaturated ring; with
the proviso that: 1) when R.sub.1 and R.sub.2 have the meanings
defined in point v), then the compounds of formula (I) do not
contain more than 3 hydroxyl radicals; 2) when R.sub.1 and R.sub.2
have the meanings defined in point v) and when R.sub.1 and R.sub.2
form a pyrrolidine ring substituted with a carbamoyl radical on the
carbon in the alpha position to the nitrogen atom to which they are
attached, then n is other than 0; or the pyrrolidine ring bears at
least two substituents; 3) when R.sub.1 and R.sub.2 have the
meanings defined in point v) and when R.sub.1 and R.sub.2 form a
pyrrolidine ring substituted with a hydroxymethyl radical on the
carbon in the alpha position relative to the nitrogen atom to which
they are attached and when n=0 or 1, then either said ring bears at
least two additional substituents, or said ring bears only one
second substituent other than a hydroxyl radical on the carbon
located in the .beta. position relative to the nitrogen atom and
relative to the carbon bearing said hydroxymethyl substituent; or
alternatively when R.sub.1 and R.sub.2 have the meanings defined in
point v) and when R.sub.1 and R.sub.2 form a pyrrolidine ring
substituted with a hydroxymethyl radical on the carbon located in
the alpha position relative to the nitrogen atom to which they are
attached, and when n=1, then R.sub.3 is other than an alkyl or
mono- or polyhydroxyalkyl radical; 4) when R.sub.1 and R.sub.2 have
the meanings defined in point iii), the compounds of formula (I)
must satisfy at least one of the following four conditions: a)
irrespective of the value of n, the alkylene ring formed by the
radical R.sub.2 comprises a substituent in addition to the radical
R.sub.1; or b) n is greater than 1; or c) when n is equal to 1,
then R.sub.3 represents an aryl radical or a heterocycle; or d)
when n is equal to 0 or 1, then R.sub.1 represents an aryl radical,
a heterocycle or a substituted alkyl radical other than a
monohydroxyalkyl radical; 5) R.sub.1 and R.sub.2 form a ring other
than piperazine or diazacycloheptane; (B) at least one alkaline
agent chosen from alkanolamines, diaminoalkanes and aqueous
ammonia, and (C) hydrogen peroxide.
2. The composition as claimed in claim 1, characterized in that, in
formula (I), R.sub.1 and R.sub.2 take one of the meanings i) to v)
below: i) R.sub.1 and R.sub.2 simultaneously represent a
--(CH.sub.2).sub.2CHOHC- H.sub.2OH radical; or ii) R.sub.1
represents a --CH.sub.2(CHOH).sub.4CH.su- b.2OH radical and R.sub.2
represents a hydrogen atom or an alkyl radical; or iv) R.sub.1
represents a radical --(CH.sub.2CH.sub.2O).sub.pR.sub.4 in which p
is an integer between 2 and 8 inclusive, R.sub.4 and R.sub.2, which
may be identical or different, represent a hydrogen atom or an
alkyl radical; v) R.sub.1 and R.sub.2 form, together with the
nitrogen atom to which they are attached, a 5-, 6- or 7-membered
saturated heterocycle, said heterocycle being substituted with at
least one radical containing at least one carbon, nitrogen or
oxygen atom, which is not in a meta position relative to the
nitrogen atom of the heterocycle; R.sub.3 represents a halogen
atom, an alkyl or aryl radical or a heterocycle, n is an integer
equal to 0, 1 or 2.
3. The composition as claimed in claim 1 or 2, characterized in
that, in formula (I), R.sub.1 and R.sub.2 form a pyrrolidine
heterocycle.
4. The composition as claimed in claim 1 or 2, characterized in
that the substituted para-phenylenediamine derivative(s) of formula
(I) is (are) chosen from:
1-N,N-bis(3',4'-dihydroxybutyl)-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-methyl-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-ethyl-para-phenylenediamine,
1-N,N-bis-(3',4'-dihydroxybutyl)-3-propyl-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-methoxy-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-ethoxy-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-propyloxy-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-hexyloxy-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-(1"-N-3",5"-dimethylpyrazolyl-para-phen-
ylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-ureido-para-phenylenediami- ne,
1-N,N-bis(3',4'-dihydroxybutyl)-3-trimethyl-1",3",3"-ureido-para-pheny-
lenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-dimethylamino-para-phenylen-
ediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-methylthio-para-phenylenediami-
ne,
1-N,N-bis(3',4'-dihydroxybutyl)-3-ethylthio-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-mercapto-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-n-butylthio-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-n-octylthio-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-mercaptoethyl-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-mercaptoethylthio-para-phenylenediamine-
,
1-N,N-bis(3',4'-dihydroxybutyl)-3-.beta.-hydroxyethylthio-para-phenylene-
diamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-methyl-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-isopropyl-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-methoxy-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-1-N-(4"-N"-methylpiperidyl)-3-etho-
xy-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-isoprop-
yloxy-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-dime-
thylamino-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3--
methylthio-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-
-mercapto-para-phenylenediamine,
1-N-(hexyl)-1-N-(2',3',4',5',6'-pentahydr-
oxyhexyl)-3-isopropyl-para-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5'-
,6'-pentahydroxyhexyl)-3-isooctyloxy-para-phenylenediamine,1-N-(methyl)-1--
N-(2',3',4',5',6'-pentahydroxyhexyl)-3-isopropyloxy-para-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-methyl-para-phenyle-
nediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-ethyl-par-
a-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3--
hydroxyethyloxy-para-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pe-
ntahydroxyhexyl)-3-mercaptoethyloxy-para-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-para-phenylenediamine-
,
1-N-(phenyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-ethyloxy-para-phen-
ylenediamine,
1-N-(4"-N-methylpiperidyl)-1-N-(2',3',4',5',6'-pentahydroxyh-
exyl)-3-ethyloxy-para-phenylenediamine,
4-N-(methyl)-4-N-(2',3',4',5',6'-p-
entahydroxyhexyl)-amino-7-amino-1-methylindole,
1-N-(hydroxyethyloxyethyl)-
-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-ethyl-para-phenylenediamine,
1-N-(3',4'-dihydroxybutyl)-5-aminoindoline,
1-(2'-hydroxyethyl)-2-methyl-- 5-aminoindoline,
1-methyl-2-hydroxymethyl-5-aminoindoline,
6-methyl-2-hydroxyethyl-5-aminoindoline,
2-hydroxyethyloxyethyl-5-aminoin- doline,
2-hydroxyethyloxyethyloxyethyloxyethyl-5-aminoindoline,
2-hydroxyethyloxyethyloxyethyl-oxyethyloxyethyloxyethyl-6-isopropyl-5-ami-
noindoline, 2-hydroxyethyl-3-methyl-5-aminoindoline,
2-hydroxyethyloxyethyloxyethyl)-5-aminoindoline,
1-carboxymethyl-2,3,3-tr- imethyl-5-aminoindoline,
1-methylsulfonamidoethyl-3-methyl-5-aminoindoline- ,
1-ureidoethyl-6-methoxy-5-aminoindoline,
1-(2',3',4',5',6'-pentahydroxyh- exyl)-5-aminoindoline,
1-N-(2'-mercaptoethyl)-5-aminoindoline, the dimethyl ester
6-amino-1-methyl-1,2,3,4-tetrahydrofuro-[2,3,h]-quinoline 4-methyl
ester of phosphoric acid, 6-amino-1,2,2-trimethyl-4-trimethylsil-
anyloxy-1,2,3,4-tetrahydroquinoline,
6-amino-1-hexyl-2,2,7-trimethyl-4-mer-
captomethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(3',4'-dihydroxybutyl)--
2,2,3-trimethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(ethoxyethoxyethoxy-
ethoxy-3',4'-dihydroxybutyl)-2,2,3,7-tetramethyl-1,2,3,4-tetrahydroquinoli-
ne,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethyl)-2,2,3-trimethyl-1,2,3-
,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyl)-2,2,3-trimethyl-1-
,2,3,4-tetrahydroquinoline,
6-amino-1-(ethylbis(hydroxyethyloxyethyloxyeth-
yloxyethyl))-2,2,3,7-tetramethyl-1,2,3,4-tetrahydroquinoline,
1-(carboxymethyl)-2,2,3,7-tetramethyl-1,2,3,4-tetrahydroquinoline,
1-(hydroxypropyl)-2,2,3-trimethyl-7-methoxy-1,2,3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyl)-2,2,3-trimethyl-7-isopropyl-1,2,-
3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethylox-
yethyloxyethyl-oxyethyloxyethyl)-2,2,3-trimethyl-7-isopropyl-1,2,3,4-tetra-
hydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethyloxyethyloxy-
ethyl-oxyethyloxyethyl)-2,2,3-trimethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(mercaptoethyl)-1,2,3,4-tetrahydroquinoline,
6-amino-1-(3',4'-dihydroxybutyl)-2,2,3-trimethyl-7-isopropyl-1,2,3,4-tetr-
ahydroquinoline,
6-amino-1-(3',4'-dihydroxybutyl)-2,2,7-trimethyl-4-hydrox-
ymethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(3',4'-dihydroxybutyl)-2,2--
dimethyl-4-hydroxymethyl-7-isopropyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(3-hydroxypropyl)-2,2-dimethyl-4-hydroxymethyl-7-isopropyl-1,2,-
3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethylox-
yethyloxy-ethyloxyethyloxyethyl)-2,2-dimethyl-4-hydroxymethyl-7-isopropyl--
1,2,3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyeth-
yl)-2,2-dimethyl-4-hydroxymethyl-7-isopropyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethyloxy-ethyl)-2,2-dimethyl-7--
isopropyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxye-
thyloxyethyloxyethyloxyethyl)-2,2-dimethyl-7-isopropyl-1,2,3,4-tetrahydroq-
uinoline,
6-amino-1-(hydroxyethyloxyethyl)-2,2-dimethyl-1,2,3,4-tetrahydro-
quinoline,
6-amino-1,2,2,4,7-pentamethyl-3-hydroxy-1,2,3,4-tetrahydroquino-
line,
6-amino-1-(3'-hydroxypropyl)-4-(hydroxyethyloxyethyloxyethyloxy-ethy-
l)-2,2-dimethyl-7-isopropyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethyl)-4,4-dimethyl-1,2,3,4-tet-
rahydroquinoline,
6-amino-1-(3',4'-dihydroxybutyl)-2,2-dimethyl-7-isopropy-
l-1,2,3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxye-
thyl)-4-(hydroxyethyloxyethyloxyethyloxyethyl)-2,2,7-trimethyl-1,2,3,4-tet-
rahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethyl)-2,2-dim-
ethyl-7-isopropyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(2',3',4',5',6'-p-
entahydroxyhexyl)-2,2,4-trimethyl-7-isopropyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(mercaptoethyl)-2,2,4-trimethyl-7-(2',3'-dihydroxypropyloxy)-1,-
2,3,4-tetrahydroquinoline,
6-amino-1-(3',4'-dihydroxybutyl)-2,2,7-trimethy-
l-3-mercaptomethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(ureidoethyl)-2,-
2,4-trimethyl-1,2,3,4-tetrahydroquinoline,
6-amino-2,2-dimethyl-7-chloro-1-
,2,3,4-tetrahydroquinoline-1-propylsulfonic acid,
6-amino-1-(4'-pyridinyl)-
-2,2,7-trimethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(3',4'-dihydroxybu-
tyl)-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1,7-diisopropyl-2,2-dimethyl-4-trimethylsilanyloxy-1,2,3,4-tetrah-
ydroquinoline,
6-amino-1,2,2,4-tetramethyl-3-hydroxy-1,2,3,4-tetrahydroqui-
noline,
6-amino-1-bromo-2,2-dimethyl-4-mercapto-7-isopropyloxy-1,2,3,4-tet-
rahydroquinoline,
1-(4'-amino-3'-isopropyloxyphenyl)-2,6-dimethylpyrrolidi- ne,
1-(4'-amino-3'-methylphenyl)-3-hydroxyethyloxypyrrolidine,
1-(4'-amino-3'-methylphenyl)-4-hydroxy-2-methylpyrrolidine,
1-(4'-amino-3'-methylphenyl)-3-methylsulfonamidopyrrolidine,
1-(4'-amino-3'-phenoxyphenyl)-3-methylsulfonamidopyrrolidine,
3-n-butylpyrrolidine-1-(4'-amino-3'-phenylsulfonic acid),
1-(4'-amino-3'-acetylaminophenyl)-3-hydroxymethylpyrrolidine,
7-amino-4-(2'-methyl)-pyrrolidinylbenzofuran,
1-(4'-aminophenyl)-2-(4"-am- inophenoxymethyl)piperidine,
1-(4'-amino-3'-acetylphenyl)-4-hydroxypiperid- ine,
1-(4'-aminophenyl)-2-(hydroxyethyl)piperidine,
1-(4'-amino-3'-methoxyphenyl)-2,6-dihydroxymethylpiperidine,
1-(4'-amino-3'-isopropyloxyphenyl)-2,6-dimethylpiperidine,
1-(4'-amino-3'-isopropylphenyl)-2-hydroxymethylpiperidine,
1-(4'-amino-3'-isopropyloxyphenyl)-2-hydroxymethylpiperidine,
1-(4'-amino-3'-aminophenyl)-2-hydroxymethylpiperidine,
1-(4'-amino-3'-dimethylaminophenyl)-2-mercaptoethyloxyethylpiperidine,
1-(4'-amino-3'-(2"',4"'-dichloro)anilinophenyl)-4-methylpiperidine,
1-(4'-aminophenyl)-4-methylpiperidine,
1-(4'-aminophenyl)-2,7-dimethylaza- cycloheptane,
1-(4'-amino-3'-methylphenyl)-2-methylazacycloheptane,
1-(4'-amino-3'-ureidophenyl)-3-hydroxyazacycloheptane,
1-(4'-amino-3'-sulfamoylaminophenyl)-2,7-dimethylazacycloheptane,
1-(4'-amino-3'-methylthiophenyl)-2,7-dimethylazacycloheptane,
1-N-4'-hydroxybutyl-1-N-(hydroxyethyloxyethyloxyethyl)-3-isopropyl-para-p-
henylenediamine,
1-N-methyl-1-N-(hydroxyethyloxyethyloxyethyl)-para-phenyl-
enediamine,
1-N-phenyl-1-N-(hydroxyethyloxyethyl)-para-phenylenediamine,
1-N-benzyl-1-N-(hydroxyethyloxyethyloxyethyloxyethyloxyethyl)-3-trimethyl-
silyl-para-phenylenediamine,
1-N-methyl-1-N-(hydroxyethyloxyethyloxyethylo-
xyethyloxyethyloxy-ethyloxyethyloxyethyl)-3-trimethylsilyloxy-para-phenyle-
nediamine,
1-N-ethyl-1-N-(methoxyethyloxyethyloxyethyloxyethyloxyethyl)-3--
phenoxycarbonylamino-para-phenylenediamine,
1-N-methyl-1-N-(methoxyethylox-
yethyloxyethyl)-3-(2',5'-dioxopyrrolidinyl)-para-phenylenediamine,
1-N-ethyl-1-N-(hydroxyethyloxyethyloxyethyl)-3-4'-pyridinylthio-para-phen-
ylenediamine,
1-N-propyl-1-N-(hydroxyethyloxyethyloxyethyl)-3-sulfinyl-par-
a-phenylenediamine,
1-N-methyl-1-N-(hydroxyethyloxyethyl)-3-phenoxycarbony-
l-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyethyloxyethyl)-p-
ara-phenylenediamine,
1-N,N-bis(methoxyethyloxyethyloxyethyloxyethyl)-3-is-
opropyloxy-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyethyl)--
3-isopropyloxy-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyeth-
yloxyethyl)-3-isopropyl-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxyet-
hyloxyethyloxyethyl)-3-isopropyl-para-phenylenediamine,
1-N,N-bis(methoxyethyloxyethyloxyethyloxyethyloxyethyloxy-ethyloxyethyl)--
3-methoxy-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyethyloxy-
ethyloxyethyloxy-ethyloxyethyloxyethyl)-3-methyl-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyethyloxyethyl)-3-isopropyloxy-para-pheny-
lenediamine,
1-N,N-bis(hydroxyethyloxyethyl)-3-mercaptoethyl-para-phenylen-
ediamine and
1-N,N-bis(benzyloxyethyloxyethyloxyethyl)-3-isopropyl-para-ph-
enylenediamine, and the addition salts thereof with an acid.
5. The composition as claimed in claim 4, characterized in that
they are chosen from:
1-N,N-bis(3',4'-dihydroxybutyl)-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-methyl-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-ethyl-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-propyl-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-methyl-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-isopropyl-para-phenylenediamine,
1-N-(hexyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-isopropyl-para-pheny-
lenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-methyl--
para-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-
-3-ethyl-para-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydr-
oxyhexyl)-para-phenylenediamine and
1-N-(hydroxyethyloxyethyl)-1-N-(2',3',-
4',5',6'-pentahydroxyhexyl)-3-ethyl-para-phenylenediamine, and the
addition salts thereof with an acid.
6. The composition as claimed in claim 4, characterized in that
they are chosen from:
1-(4'-amino-3'-methylphenyl)-3-hydroxyethyloxypyrrolidine,
1-(4'-amino-3'-methylphenyl)-4-hydroxy-2-methylpyrrolidine,
1-(4'-amino-3'-methylphenyl)-3-methylsulfonamidopyrrolidine,
1-(4'-amino-3'-phenoxyphenyl)-3-methylsulfonamidopyrrolidine,
1-(4'-aminophenyl)-2-(4"-aminophenoxymethyl)piperidine,
1-(4'-aminophenyl)-2-hydroxyethyl)piperidine,
1-(4'-amino-3'-isopropylphe- nyl)-2-hydroxymethylpiperidine,
1-(4'-aminophenyl)-4-methylpiperidine,
1-(4'-aminophenyl)-2,7-dimethylazacycloheptane,
1-(4'-amino-3'-methylphen- yl)-2-methylazacycloheptane,
1-(4'-amino-3'-ureidophenyl)-3-hydroxyazacycl- oheptane,
1-N-4'-hydroxybutyl-1-N-(hydroxyethyloxyethyloxyethyl)-3-isoprop-
yl-para-phenylenediamine,
1-N-methyl-1-N-(hydroxyethyloxyethyloxyethyl)-pa-
ra-phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyethyloxyethyl)-para--
phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyethyloxyethyl)-3-isopro-
pyl-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyethyloxyethyl)-
-3-isopropyl-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyethyl-
oxyethyloxyethyloxy-ethyloxyethyloxyethyl)-3-methyl-para-phenylenediamine
and
1-N,N-bis(benzyloxyethyloxyethyloxyethyl)-3-isopropyl-para-phenylened-
iamine.
7. The composition as claimed in any one of the preceding claims,
characterized in that the addition salts with an acid are chosen
from the hydrochlorides, hydrobromides, sulfates, tartrates,
lactates and acetates.
8. The composition as claimed in any one of the preceding claims,
characterized in that the substituted para-phenylenediamine
derivative(s) of formula (I) and/or the addition salt(s) thereof
with an acid represent from 0.0001% to 20% by weight relative to
the total weight of the composition.
9. The composition as claimed in claim 7, characterized in that the
substituted para-phenylenediamine derivative(s) of formula (I)
and/or the addition salt(s) thereof with an acid represent from
0.001% to 15% by weight relative to the total weight of the
composition.
10. The composition as claimed in claim 9, characterized in that
the substituted para-phenylenediamine derivative(s) of formula (I)
and/or the addition salt(s) thereof with an acid represent from
0.01% to 10% by weight relative to the total weight of the
composition.
11. The composition as claimed in claim 1, characterized in that
the alkanolamine is a saturated or unsaturated, linear or branched
hydrocarbon compound containing from 2 to 100 carbon atoms and
comprising (i) at least one amine function and (ii) at least one
hydroxyl function not borne by the amine function.
12. The composition as claimed in claim 11, characterized in that
the alkanolamine is a saturated hydrocarbon compound containing
from 2 to 100 carbon atoms.
13. The composition as claimed in claims 1 or 11 or 12,
characterized in that the alkanolamines are chosen from
monoethanolamine, diethanolamine, triethanolamine,
triisopropanolamine, 2-amino-2-methyl-1-propanol,
2-amino-2-methyl-1,3-propanediol, 2-amino-2-ethyl-1,3-propanediol,
2-amino-1-butanol, tris(hydroxymethyl)aminomethane,
2-aminoethylethanolamine, 1-diethylamino-2,3-propanediol,
2-dimethylamino-2-methyl-1-propanol, dimethylethanolamine,
diethylethanolamine, ethylmonoethanolamine and
methylethanolamine.
14. The composition as claimed in claim 13, characterized in that
the alkanolamine is monoethanolamine.
15. The composition as claimed in claim 1, characterized in that
the diaminoalkanes are of formula (II): 4in which W is an alkylene
residue optionally substituted with a hydroxyl group or a
C.sub.1-C.sub.4 alkyl radical; R.sub.5, R.sub.6, R.sub.7 and
R.sub.8, which may be identical or different, represent a hydrogen
atom or a C.sub.1-C.sub.4 alkyl or C.sub.1-C.sub.4 hydroxyalkyl
radical.
16. The composition as claimed in claim 15, characterized in that W
is a propylene residue.
17. The composition as claimed in claim 16, characterized in that
the diaminoalkane is diaminopropane.
18. The composition as claimed in claim 1, characterized in that
the alkaline agent is aqueous ammonia.
19. The composition as claimed in any one of the preceding claims,
characterized in that the alkaline agent(s) is (are) present in
concentrations ranging from 0.1% to 20% by weight of active
material relative to the total weight of the composition.
20. The composition as claimed in claim 19, characterized in that
the alkaline agent(s) is (are) present in concentrations ranging
from 0.5% to 10% by weight of active material relative to the total
weight of the composition.
21. The composition as claimed in any one of the preceding claims,
characterized in that the hydrogen peroxide is present in a
concentration of between 0.5% and 15% by weight relative to the
total weight of the composition.
22. The composition as claimed in claim 21, characterized in that
the hydrogen peroxide is present in a concentration of between 1%
and 10% by weight relative to the total weight of the
composition.
23. The composition as claimed in any one of the preceding claims,
characterized in that it contains at least one coupler.
24. The composition as claimed in claim 23, characterized in that
the coupler(s) is (are) chosen from meta-phenylenediamines,
meta-aminophenols, meta-diphenols and heterocyclic couplers, such
as, for example, indole derivatives, indoline derivatives,
benzimidazole derivatives, benzomorpholine derivatives, sesamol
derivatives and pyridine, pyrimidine and pyrazole derivatives, and
the addition salts thereof with an acid.
25. The composition as claimed in claim 24, characterized in that
the coupler(s) is (are) chosen from 2-methyl-5-aminophenol,
5-N-(.beta.-hydroxyethyl)amino-2-methylphenol, 3-aminophenol,
1,3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene,
4-chloro-1,3-dihydroxybenzene,
2,4-diamino-1-(.beta.-hydroxyethyloxy)benz- ene,
2-amino-4-(.beta.-hydroxyethylamino)-1-methoxybenzene,
1,3-diaminobenzene, 1,3-bis(2,4-diaminophenoxy)propane, sesamol,
1-amino-2-methoxy-4,5-methylenedioxybenzene, .alpha.-naphthol,
2-methyl-1-naphthol, 6-hydroxyindole, 4-hydroxyindole,
4-hydroxy-N-methylindole, 6-hydroxyindoline,
2,6-dihydroxy-4-methylpyridi- ne, 1-H-3-methylpyrazol-5-one and
1-phenyl-3-methylpyrazol-5-one, and the addition salts thereof with
an acid.
26. The composition as claimed in any one of claims 13 to 25,
characterized in that the coupler(s) is (are) present in a
concentration of between 0.0001% and 15% by weight relative to the
total weight of the composition.
27. The composition as claimed in any one of the preceding claims,
characterized in that it contains at least one additional oxidation
base and/or at least one direct dye.
28. The composition as claimed in claim 27, characterized in that
the additional oxidation base(s) is (are) chosen from
para-phenylenediamine, para-tolylenediamine,
2-hydroxyethyl-para-phenylenediamine,
1-N,N-bis(2-hydroxyethyl)-para-phenylenediamine, para-aminophenols,
ortho-phenylenediamines, ortho-aminophenols, double bases and
heterocyclic bases.
29. The composition as claimed in claims 27 and 28, characterized
in that the additional oxidation base(s) is (are) present in a
concentration of between 0.0001% and 15% by weight relative to the
total weight of the composition.
30. The composition as claimed in any one of the preceding claims,
characterized in that the medium that is suitable for dyeing
consists of water or of a mixture of water and at least one organic
solvent.
31. The composition as claimed in claim 30, characterized in that
the solvents are present in proportions of between 1% and 40% by
weight relative to the total weight of the composition.
32. The composition as claimed in any one of the preceding claims,
characterized in that it contains anionic, cationic, nonionic,
amphoteric or zwitterionic surfactants or mixtures thereof,
anionic, cationic, nonionic, amphoteric or zwitterionic polymers or
mixtures thereof, mineral or organic thickeners, thickening
polymers, antioxidants, penetrating agents, sequestering agents,
fragrances, buffers, dispersants, conditioners such as, for
example, volatile or non-volatile silicones, which are modified or
unmodified, film-forming agents, ceramides, preserving agents and
opacifiers.
33. The composition as claimed in claim 32, characterized in that
it contains at least one cationic polymer in a proportion of from
0.05% to 10% by weight and at least one nonionic surfactant in a
proportion of from 0.1% to 20% by weight.
34. The composition as claimed in claim 32, characterized in that
it contains at least one thickening polymer comprising at least one
hydrophilic unit and at least one fatty chain in a proportion of
from 0.05% to 10% by weight.
35. The composition as claimed in any one of the preceding claims,
characterized in that the pH is greater than 7 and preferably
greater than 8.
36. The composition as claimed in any one of the preceding claims,
characterized in that it is in the form of liquid, powder, cream or
gel, which are optionally pressurized, or in any other form that is
suitable for dyeing keratin fibers.
37. A composition intended for the oxidation dyeing of keratin
fibers, and in particular of human keratin fibers such as the hair,
comprising, in a medium that is suitable for dyeing, at least one
substituted para-phenylenediamine derivative of formula (I) defined
in any one of claims 1 to 6, and at least one alkaline agent
defined in any one of claims 1 and 11 to 18.
38. A process for dyeing keratin fibers, and in particular human
keratin fibers such as the hair, characterized in that a dye
composition containing, in a medium that is suitable for dyeing, at
least one substituted para-phenylenediamine derivative of formula
(I) defined in any one of claims 1 to 6 is mixed, at the time of
use, with an oxidizing composition containing, in a medium that is
suitable for dyeing, at least hydrogen peroxide, the alkaline
agent(s) defined in any one of claims 1 and 11 to 18 being present
in one or both of the compositions, the mixture obtained is applied
to the keratin fibers and is left in place for 3 to 50 minutes,
after which the fibers are rinsed, washed with shampoo, rinsed
again and dried.
39. A multi-compartment dyeing device or "kit" comprising at least
one compartment containing a dye composition containing at least
one substituted para-phenylenediamine derivative of formula (I)
defined in any one of claims 1 to 6, and another compartment
containing an oxidizing composition containing hydrogen peroxide,
the alkaline agent(s) defined in any one of claims 1 and 11 to 18
being present in one or both of the compositions.
Description
[0001] The invention relates to a ready-to-use composition for the
oxidation dyeing of keratin fibers, and in particular of human
keratin fibers such as the hair, comprising, in a medium that is
suitable for dyeing, at least one oxidation base chosen from
certain substituted para-phenylenediamine derivatives and the
addition salts thereof with an acid, at least one selected alkaline
agent and hydrogen peroxide, and also to the dyeing process using
this composition.
[0002] It is known practice to dye keratin fibers, and in
particular human hair, with dye compositions containing oxidation
dye precursors, in particular ortho- or para-phenylenediamines,
ortho- or para-aminophenols, and heterocyclic bases, which are
generally known as oxidation bases. These oxidation dye precursors
(oxidation bases) are colorless or weakly colored compounds which,
when combined with oxidizing products, can give rise to colored
compounds and dyes by a process of oxidative condensation.
[0003] It is also known that the shades obtained with these
oxidation bases can be varied by combining them with couplers or
coloration modifiers, the latter being chosen in particular from
aromatic meta-diamines, meta-aminophenols, meta-diphenols and
certain heterocyclic compounds.
[0004] The variety of molecules used as oxidation bases and
couplers allows a wide range of colors to be obtained.
[0005] The so-called "permanent" coloration obtained by means of
these oxidation dyes should moreover satisfy a certain number of
requirements. Thus, it should allow shades to be obtained in the
desired intensity and it should have good staying power with
respect to external agents (light, bad weather, washing,
permanent-waving, perspiration or rubbing).
[0006] The dyes should also allow gray hair to be covered and,
finally, they should be as unselective as possible, i.e. they
should allow only the smallest possible differences in coloration
to be obtained along the same keratin fiber, which may indeed be
differently sensitized (i.e. damaged) between its end and its
root.
[0007] It has already been proposed, especially in patent
applications JP-11-158 046, JP-11-158 047 and JP-11-158 048 to use
compositions for the oxidation dyeing of keratin fibers, containing
substituted para-phenylenediamine derivatives as oxidation dye
precursors. However, the colorations obtained by using these
compositions are not always sufficiently intense, chromatic or
resistant to the various attacking factors to which the hair may be
subjected.
[0008] However, the Applicant has now discovered that it is
possible to obtain novel dyes, which are capable of giving
chromatic, intense, attractive colorations in varied shades, which
are relatively unselective and resistant to the various attacking
factors to which the fibers may be subjected, by combining at least
one oxidation base chosen from certain para-phenylenediamine
derivatives of formula (I) defined below and the addition salts
thereof with an acid, at least one selected alkaline agent and
hydrogen peroxide.
[0009] This discovery forms the basis of the present invention.
[0010] Thus, a first subject of the invention is a ready-to-use
composition for the oxidation dyeing of keratin fibers, in
particular of human keratin fibers such as the hair, characterized
in that it comprises, in a medium that is suitable for dyeing:
[0011] (A) at least one oxidation base chosen from the substituted
para-phenylenediamine derivatives of formula (I) below, and the
addition salts thereof with an acid: 1
[0012] in which:
[0013] R.sub.1 and R.sub.2 can take one of the following meanings
i) to v) below:
[0014] i) R.sub.1 and R.sub.2 simultaneously represent a
--(CH.sub.2).sub.2CHOHCH.sub.2OH radical; or
[0015] ii) R.sub.1 represents a --CH.sub.2(CHOH).sub.4CH.sub.2OH
radical and R.sub.2 represents a hydrogen atom, an alkyl or aryl
radical or a heterocycle; or
[0016] iii) R.sub.1 represents an alkyl or aryl radical or a
heterocycle and R.sub.2 represents an alkylene radical
--(CH.sub.2).sub.m-- in which m is an integer equal to 2 or 3, said
alkylene radical forming a ring together with the nitrogen atom,
the carbon atom of the benzene ring bearing the nitrogen atom and
one of the two carbon atoms of the benzene ring that are adjacent
to it, it being understood that when R.sub.1 is an alkyl or aryl
radical, then either R.sub.1 or said alkylene radical is
substituted with a radical containing at least one nitrogen, oxygen
or sulfur atom;
[0017] iv) R.sub.1 represents a radical
--(CH.sub.2CH.sub.2O).sub.pR.sub.4 in which p is an integer between
2 and 8 inclusive, R.sub.4 and R.sub.2, which may be identical or
different, represent a hydrogen atom, an alkyl or aryl radical or a
heterocycle;
[0018] v) R.sub.1 and R.sub.2 form, together with the nitrogen atom
to which they are attached, a 5-, 6- or 7-membered saturated
heterocycle, said heterocycle being substituted with at least one
radical containing at least one carbon, nitrogen, oxygen or sulfur
atom;
[0019] R.sub.3 represents a halogen atom, an alkyl or aryl radical,
a cyano, nitro, hydroxyl, carboxyl, sulfo, alkoxy, aryloxy,
cyanoamino, amino, anilino, ureido, sulfamylamino, mono- or
dialkylsulfamylamino, alkylthio, arylthio, alkoxycarbonylamino,
sulfonamido, carbamyl, mono- or dialkylcarbamylsulfamyl, sulfonyl,
alkoxycarbonyl, azo, acyloxy, carbamyloxy, mono- or
dialkylcarbamyloxy, silyl, silyloxy, aryloxycarbonylamino, imido,
sulfinyl, phosphonyl, aryloxycarbonyl, acyl or mercapto radical, a
heterocycle or a heterocycle linked to the benzene ring of formula
(I) via an ether or thio bond;
[0020] said alkyl radicals containing from 1 to 25 carbon atoms and
possibly being linear, branched or cyclic and possibly being
substituted with one or more radicals, and in this case possibly
representing a mono- or polyhydroxyalkyl radical, an alkoxyalkyl
radical, an aminoalkyl radical optionally substituted on the
nitrogen atom, or a carboxyalkyl, alkylcarboxyalkyl, thioalkyl,
alkylthioalkyl, cyanoalkyl, trifluoroalkyl, sulfoalkyl,
phosphoalkyl or haloalkyl radical;
[0021] said alkoxy radicals containing from 1 to 25 carbon atoms
and possibly being linear, branched or cyclic;
[0022] said aryl radicals containing from 6 to 26 carbon atoms and
possibly being substituted with one or more radicals chosen from
alkyl, substituted alkyl and alkoxy radicals;
[0023] the heterocycles being monocyclic or polycyclic, each ring
being 3-, 4-, 5- or 6-membered and possibly containing one or more
hetero atoms, it being understood that in the case of polycyclic
heterocycles, at least one of the rings contains at least one
hetero atom such as N, O or S;
[0024] n is an integer between 0 and 4; it being understood that
when n is greater than 1, then the radicals R.sub.3 may be
identical or different and may together form a 3-, 4-, 5- or
6-membered saturated or unsaturated ring; with the proviso
that:
[0025] 1) when R.sub.1 and R.sub.2 have the meanings defined in
point v), then the compounds of formula (I) do not contain more
than 3 hydroxyl radicals;
[0026] 2) when R.sub.1 and R.sub.2 have the meanings defined in
point v) and when R.sub.1 and R.sub.2 form a pyrrolidine ring
substituted with a carbamoyl radical on the carbon in the position
alpha to the nitrogen atom to which they are attached, then n is
other than 0; or the pyrrolidine ring bears at least two
substituents;
[0027] 3) when R.sub.1 and R.sub.2 have the meanings defined in
point v) and when R.sub.1 and R.sub.2 form a pyrrolidine ring
substituted with a hydroxymethyl radical on the carbon in the alpha
position relative to the nitrogen atom to which they are attached
and when n=0 or 1, then either said ring bears at least two
additional substituents, or said ring bears only one second
substituent other than a hydroxyl radical on the carbon located in
the .beta. position relative to the nitrogen atom and relative to
the carbon bearing said hydroxymethyl substituent; or
alternatively, when R.sub.1 and R.sub.2 have the meanings defined
in point v) and when R.sub.1 and R.sub.2 form a pyrrolidine ring
substituted with a hydroxymethyl radical on the carbon located in
the alpha position relative to the nitrogen atom to which they are
attached, and when n=1, then R.sub.3 is other than an alkyl or
mono- or polyhydroxyalkyl radical;
[0028] 4) when R.sub.1 and R.sub.2 have the meanings defined in
point iii), the compounds of formula (I) must satisfy at least one
of the following four conditions:
[0029] a) irrespective of the value of n, the alkylene ring formed
by the radical R.sub.2 comprises a substituent in addition to the
radical R.sub.1; or
[0030] b) n is greater than 1; or
[0031] c) when n is equal to 1, then R.sub.3 represents an aryl
radical or a heterocycle; or
[0032] d) when n is equal to 0 or 1, then R.sub.1 represents an
aryl radical, a heterocycle or a substituted alkyl radical other
than a monohydroxyalkyl radical;
[0033] 5) R.sub.1 and R.sub.2 form a ring other than piperazine or
diazacycloheptane;
[0034] (B) at least one alkaline agent chosen from alkanolamines,
diaminoalkanes and aqueous ammonia, and
[0035] (C) hydrogen peroxide.
[0036] The addition salts with an acid of the substituted
para-phenylenediamine derivatives of formula (I) that may be used
in the dye compositions according to the present invention are
chosen especially from the hydrochlorides, hydrobromides, sulfates,
tartrates, lactates and acetates.
[0037] The ready-to-use dye composition in accordance with the
invention gives chromatic, intense, attractive colorations in
varied shades, with low selectivity and excellent resistance
properties not only with respect to atmospheric agents such as
light and bad weather, but also with respect to perspiration and
the various treatments to which the hair may be subjected.
[0038] For the purposes of the invention, the. expression
"ready-to-use composition" means any composition intended to be
applied immediately to keratin fibers.
[0039] A subject of the invention is also a process for the
oxidation dyeing of keratin fibers using said composition.
[0040] Another subject of the invention is a multi-compartment
dyeing device or "kit".
[0041] A subject of the invention is also a composition for the
oxidation dyeing of keratin fibers, and in particular of human
keratin fibers such as the hair, comprising, in a medium that is
suitable for dyeing, at least one substituted para-phenylenediamine
derivative of formula (I) and at least one alkaline agent chosen
from alkanolamines, diaminoalkanes and aqueous ammonia.
[0042] According to the present invention, the substituted
para-phenylenediamine derivatives that are preferably used are
those of formula (I) above in which:
[0043] R.sub.1 and R.sub.2 can take one of the meanings i) to v)
below:
[0044] i) R.sub.1 and R.sub.2 simultaneously represent a
--(CH.sub.2).sub.2CHOHCH.sub.2OH radical; or
[0045] ii) R.sub.1 represents a --CH.sub.2(CHOH).sub.4CH.sub.2OH
radical and R.sub.2 represents a hydrogen atom or an alkyl radical;
or
[0046] iv) R.sub.1 represents a radical
--(CH.sub.2CH.sub.2O).sub.pR.sub.4 in which p is an integer between
2 and 8 inclusive, R.sub.4 and R.sub.2, which may be identical or
different, represent a hydrogen atom or an alkyl radical;
[0047] v) R.sub.1 and R.sub.2 form, together with the nitrogen atom
to which they are attached, a 5-, 6- or 7-membered saturated
heterocycle, said heterocycle being substituted with at least one
radical containing at least one carbon, nitrogen or oxygen atom,
which is not in a meta position relative to the nitrogen atom of
the heterocycle;
[0048] R.sub.3 represents a halogen atom, an alkyl or aryl radical
or a heterocycle,
[0049] n is an integer equal to 0, 1 or 2.
[0050] More particularly, according to the invention, in formula
(I), R.sub.1 and R.sub.2 form a pyrrolidine heterocycle.
[0051] Among the substituted para-phenylenediamine derivatives of
formula (I) above that may be mentioned most particularly are
1-N,N-bis(3',4'-dihydroxybutyl)-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-methyl-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-ethyl-para-phenylenediamine,
1-N,N-bis-(3',4'-dihydroxybutyl)-3-propyl-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-methoxy-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-ethoxy-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-propyloxy-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-hexyloxy-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-(1"-N-3",5"-dimethylpyrazolyl-para-phen-
ylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-ureido-para-phenylenediami- ne,
1-N,N-bis(3',4'-dihydroxybutyl)-3-trimethyl-1",3",3"-ureido-para-pheny-
lenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-dimethylamino-para-phenylen-
ediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-methylthio-para-phenylenediami-
ne,
1-N,N-bis(3',4'-dihydroxybutyl)-3-ethylthio-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-mercapto-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-n-butylthio-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-n-octylthio-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-mercaptoethyl-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-mercaptoethylthio-para-phenylenediamine-
,
1-N,N-bis(3',4'-dihydroxybutyl)-3-.beta.-hydroxyethylthio-para-phenylene-
diamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-methyl-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-isopropyl-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-methoxy-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-1-N-(4"-N"-methylpiperidyl)-3-etho-
xy-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-isoprop-
yloxy-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-dime-
thylamino-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3--
methylthio-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-
-mercapto-para-phenylenediamine,
1-N-(hexyl)-1-N-(2',3',4',5',6'-pentahydr-
oxyhexyl)-3-isopropyl-para-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5'-
,6'-pentahydroxyhexyl)-3-isooctyloxy-para-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-isopropyloxy-para-p-
henylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-met-
hyl-para-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydroxyhe-
xyl)-3-ethyl-para-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-penta-
hydroxyhexyl)-3-hydroxyethyloxy-para-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-mercaptoethyloxy-pa-
ra-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-p-
ara-phenylenediamine,
1-N-(phenyl)-1-N-(2',3',4',5',6'pentahydroxyhexyl)-3-
-ethyloxy-para-phenylenediamine,
1-N-(4"-N-methylpiperidyl)-1-N-(2',3',4',-
5',6'-pentahydroxyhexyl)-3-ethyloxy-para-phenylenediamine,
4-N-(methyl)-4-N-(2',3',4',5',6'-pentahydroxyhexyl)-amino-7amino-1-methyl-
indole and
1-N-(hydroxyethyloxyethyl)-1-N-(2',3',4',5',6'-pentahydroxyhexy-
l)-3-ethyl-para-phenylenediamine, and the addition salts thereof
with an acid, and among which, the ones that are even more
particularly preferred are:
1-N,N-bis(3',4'-dihydroxybutyl)-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-methyl-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-ethyl-para-phenylenediamine,
1-N,N-bis(3',4'-dihydroxybutyl)-3-propyl-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-methyl-para-phenylenediamine,
1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-isopropyl-para-phenylenediamine,
1-N-(hexyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-isopropyl-para-pheny-
lenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-methyl--
para-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydroxyhexyl)-
-3-ethyl-para-phenylenediamine,
1-N-(methyl)-1-N-(2',3',4',5',6'-pentahydr-
oxyhexyl)-para-phenylenediamine and
1-N-(hydroxyethyloxyethyl)-1-N-(2',3',-
4',5',6'-pentahydroxyhexyl)-3-ethyl-para-phenylenediamine, and the
addition salts thereof with an acid.
[0052] Mention may also be made most particularly of
1-N-(3',4'-dihydroxybutyl)-5-aminoindoline,
1-(2'-hydroxyethyl)-2-methyl-- 5-aminoindoline,
1-methyl-2-hydroxymethyl-5-aminoindoline,
6-methyl-2-hydroxyethyl-5-aminoindoline,
2-hydroxyethyloxyethyl-5-aminoin- doline,
2-hydroxyethyloxyethyloxyethyloxyethyl-5-aminoindoline,
2-hydroxyethyloxyethyloxyethyloxy-ethyloxyethyloxyethyl-6-isopropyl-5-ami-
noindoline, 2-hydroxyethyl-3-methyl-5-aminoindoline,
2-hydroxyethyloxyethyloxyethyl)-5-aminoindoline,
1-carboxymethyl-2,3,3-tr- imethyl-5-aminoindoline,
1-methylsulfonamidoethyl-3-methyl-5-aminoindoline- ,
1-ureidoethyl-6-methoxy-5-aminoindoline,
1-(2',3',4',5',6'-pentahydroxyh- exyl)-5-aminoindoline,
1-N-(2'-mercaptoethyl)-5-aminoindoline, the dimethyl ester
6-amino-1-methyl-1,2,3,4-tetrahydrofuro-[2,3,h]-quinoline 4-methyl
ester of phosphoric acid, 6-amino-1,2,2-trimethyl-4-trimethylsil-
anyloxy-1,2,3,4-tetrahydroquinoline,
6-amino-1-hexyl-2,2,7-trimethyl-4-mer-
captomethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(3',4'-dihydroxybutyl)--
2,2,3-trimethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(ethoxyethoxy-ethox-
yethoxy-3',4'-dihydroxybutyl)-2,2,3,7-tetramethyl-1,2,3,4-tetrahydroquinol-
ine,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethyl)-2,2,3-trimethyl-1,2,-
3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyl)-2,2,3-trimethyl--
1,2,3,4-tetrahydroquinoline,
6-amino-1-(ethylbis-(hydroxyethyloxyethyloxye-
thyloxyethyl))-2,2,3,7-tetramethyl-1,2,3,4-tetrahydroquinoline,
1-(carboxymethyl)-2,2,3,7-tetramethyl-1,2,3,4-tetrahydroquinoline,
1-(hydroxypropyl)-2,2,3-trimethyl-7-methoxy-1,2,3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyl)-2,2,3-trimethyl-7-isopropyl-1,2,-
3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethylox-
yethyloxyethyloxyethyloxyethyl)-2,2,3-trimethyl-7-isopropyl-1,2,3,4-tetrah-
ydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethyloxyethyloxye-
thyloxyethyloxyethyl)-2,2,3-trimethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(mercaptoethyl)-1,2,3,4-tetrahydroquinoline,
6-amino-1-(3',4'-dihydroxybutyl)-2,2,3-trimethyl-7-isopropyl-1,2,3,4-tetr-
ahydroquinoline,
6-amino-1-(3',4'-dihydroxybutyl)-2,2,7-trimethyl-4-hydrox-
ymethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(3',4'-dihydroxybutyl)-2,2--
dimethyl-4-hydroxymethyl-7-isopropyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(3-hydroxypropyl)-2,2-dimethyl-4-hydroxymethyl-7-isopropyl-1,2,-
3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethylox-
yethyloxyethyloxyethyloxyethyl)-2,2-dimethyl-4-hydroxymethyl-7-isopropyl-1-
,2,3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethy-
l)-2,2-dimethyl-4-hydroxymethyl-7isopropyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethyloxyethyl)-2,2-dimethyl-7-i-
sopropyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyet-
hyloxyethyloxyethyloxyethyl)-2,2-dimethyl-7-isopropyl-1,2,3,4-tetrahydroqu-
inoline,
6-amino-1-(hydroxyethyloxyethyl)-2,2-dimethyl-1,2,3,4-tetrahydroq-
uinoline,
6-amino-1,2,2,4,7-pentamethyl-3-hydroxy-1,2,3,4-tetrahydroquinol-
ine, 6-amino-1-(3'-hydroxypropyl)
-4-(hydroxyethyloxyethyloxyethyloxy-ethy-
l)-2,2-dimethyl-7-isopropyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethyl)-4,4-dimethyl-1,2,3,4-tet-
rahydroquinoline,
6-amino-1-(3',4'-dihydroxybutyl)-2,2-dimethyl-7-isopropy-
l-1,2,3,4-tetrahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxye-
thyl)-4-(hydroxyethyloxyethyloxyethyloxyethyl)-2,2,7-trimethyl-1,2,3,4-tet-
rahydroquinoline,
6-amino-1-(hydroxyethyloxyethyloxyethyloxyethyl)-2,2-dim-
ethyl-7-isopropyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(2',3',4',5',6'-p-
entahydroxyhexyl)-2,2,4-trimethyl-7-isopropyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(mercaptoethyl)-2,2,4-trimethyl-7-(2',3'-dihydroxypropyloxy)-1,-
2,3,4-tetrahydroquinoline,
6-amino-1-(3',4'-dihydroxybutyl)-2,2,7-trimethy-
l-3-mercaptomethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(ureidoethyl)-2,-
2,4-trimethyl-1,2,3,4-tetrahydroquinoline,
6-amino-2,2-dimethyl-7-chloro-1-
,2,3,4-tetrahydroquinoline-1-propylsulfonic acid,
6-amino-1-(4'-pyridinyl)-
-2,2,7-trimethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1-(3',4'-dihydroxybu-
tyl)-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline,
6-amino-1,7-diisopropyl-2,2-dimethyl-4-trimethylsilanyloxy-1,2,3,4-tetrah-
ydroquinoline,
6-amino-1,2,2,4-tetramethyl-3-hydroxy-1,2,3,4-tetrahydroqui- noline
and
6-amino-1-bromo-2,2-dimethyl-4-mercapto-7-isopropyloxy-1,2,3,4--
tetrahydroquinoline, and the addition salts thereof with an
acid.
[0053] Mention may also be made most particularly of
1-(4'-amino-3'-isopropyloxyphenyl)-2,6-dimethylpyrrolidine,
1-(4'-amino-3'-methylphenyl)-3-hydroxyethyloxypyrrolidine,
1-(4'-amino-3'-methylphenyl)-4-hydroxy-2-methylpyrrolidine,
1-(4'-amino-3'-methylphenyl)-3-methylsulfonamidopyrrolidine,
1-(4'-amino-3'-phenoxyphenyl)-3-methylsulfonamidopyrrolidine,
3-n-butylpyrrolidine-1-(4'-amino-3'-phenylsulfonic acid),
1-(4'-amino-3'-acetylaminophenyl)-3-hydroxymethylpyrrolidine,
7-amino-4-(2'-methyl)-pyrrolidinylbenzofuran,
1-(4'-aminophenyl)-2-(4"-am- inophenoxymethyl)piperidine,
1-(4'-amino-3'-acetylphenyl)-4-hydroxypiperid- ine,
1-(4'-aminophenyl)-2-(hydroxyethyl)piperidine,
1-(4'-amino-3'-methoxyphenyl)-2,6-dihydroxymethylpiperidine,
1-(4'-amino-3'-isopropyloxyphenyl)-2,6-dimethylpiperidine,
1-(4'-amino-3'-isopropylphenyl)-2-hydroxymethylpiperidine,
1-(4'-amino-3'-isopropyloxyphenyl)-2-hydroxymethylpiperidine,
1-(4'-amino-3'-aminophenyl)-2-hydroxymethylpiperidine,
1-(4'-amino-3'-dimethylaminophenyl)-2-mercaptoethyloxyethylpiperidine,
1-(4'-amino-3'-(2"',4"'-dichloro)anilinophenyl)-4-methylpiperidine,
1-(4'-aminophenyl)-4-methylpiperidine,
1-(4'-aminophenyl)-2,7-dimethylaza- cycloheptane,
1-(4'-amino-3'-methylphenyl)-2-methylazacycloheptane,
1-(4'-amino-3'-ureidophenyl)-3-hydroxyazacycloheptane,
1-(4'-amino-3'-sulfamoylaminophenyl)-2,7-dimethylazacycloheptane,
1-(4'-amino-3'-methylthiophenyl)-2,7-dimethylazacycloheptane,
1-N-4'-hydroxybutyl-1-N-(hydroxyethyloxyethyloxyethyl)-3-isopropyl-para-p-
henylenediamine,
1-N-methyl-1-N-(hydroxyethyloxyethyloxyethyl)-para-phenyl-
enediamine,
1-N-phenyl-1-N-(hydroxyethyloxyethyl)-para-phenylenediamine,
1-N-benzyl-1-N-(hydroxyethyloxyethyloxyethyloxyethyloxyethyl)-3-trimethyl-
silyl-para-phenylenediamine,
1-N-methyl-1-N-(hydroxyethyloxyethyloxyethylo-
xyethyloxyethyloxy-ethyloxyethyloxyethyl)-3-trimethylsilyloxy-para-phenyle-
nediamine,
1-N-ethyl-1-N-(methoxyethyloxyethyloxyethyloxyethyloxyethyl)-3--
phenoxycarbonylamino-para-phenylenediamine,
1-N-methyl-1-N-(methoxyethylox-
yethyloxyethyl)-3-(2',5'-dioxopyrrolidinyl)-para-phenylenediamine,
1-N-ethyl-1-N-(hydroxyethyloxyethyloxyethyl)-3-4'-pyridinylthio-para-phen-
ylenediamine,
1-N-propyl-1-N-(hydroxyethyloxyethyloxyethyl)-3-sulfinyl-par-
a-phenylenediamine,
1-N-methyl-1-N-(hydroxyethyloxyethyl)-3-phenoxycarbony-
l-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyethyloxyethyl)-p-
ara-phenylenediamine,
1-N,N-bis(methoxyethyloxy-ethyloxyethyloxyethyl)-3-i-
sopropyloxy-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxy-ethyloxyethyl-
)-3-isopropyloxy-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxye-
thyloxyethyl)-3-isopropyl-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxy-
ethyloxyethyloxyethyl)-3-isopropyl-para-phenylenediamine,
1-N,N-bis(methoxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyl)-3-
-methoxy-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxy-ethyloxyethyloxy-
ethyloxyethyloxyethyloxyethyloxyethyl)-3-methyl-para-phenylenediamine,
1,N,N-bis(hydroxyethyloxyethyloxyethyloxyethyl)-3-isopropyloxy-para-pheny-
lenediamine,
1-N,N-bis(hydroxyethyloxyethyl)-3-mercaptoethyl-para-phenylen-
ediamine and
1-N,N-bis(benzyloxyethyloxyethyloxyethyl)-3-isopropyl-para-ph-
enylenediamine, and the addition salts thereof with an acid, and
among which, the ones that are even more particularly preferred
are: 1-(4'-amino-3'-methylphenyl)-3-hydroxyethyloxypyrrolidine,
1-(4'-amino-3'-methylphenyl)-4-hydroxy-2-methylpyrrolidine,
1-(4'-amino-3'-methylphenyl)-3-methylsulfonamidopyrollidine,
1-(4'-amino-3'-phenoxyphenyl)-3-methylsulfonamidopyrrolidine,
1-(4'-aminophenyl)-2-(4"-aminophenoxymethyl)piperidine,
1-(4'-aminophenyl)-2-hydroxyethyl)piperidine,
1-(4'-amino-3'-isopropylphe- nyl)-2-hydroxymethylpiperidine,
1-(4'-aminophenyl)-4-methylpiperidine,
1-(4'-aminophenyl)-2,7-dimethylazacycloheptane,
1-(4'-amino-3'-methylphen- yl)-2-methylazacycloheptane,
1-(4'-amino-3'-ureidophenyl)-3-hydroxyazacycl- oheptane,
1-N-4'-hydroxybutyl-1-N-(hydroxyethyloxyethyloxyethyl)-3-isoprop-
yl-para-phenylenediamine,
1-N-methyl-1-N-(hydroxyethyloxyethyloxyethyl)-pa-
ra-phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyethyloxyethyl)-para--
phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyethyloxyethyl)-3-isopro-
pyl-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyethyloxyethyl)-
-3-isopropyl-para-phenylenediamine,
1-N,N-bis(hydroxyethyloxyethyloxyethyl-
oxyethyloxyethyloxy-ethyloxyethyloxyethyl)-3-methyl-para-phenylenediamine
and
1-N,N-bis(benzyloxyethyloxyethyloxyethyl)-3-isopropyl-para-phenylened-
iamine, and the addition salts thereof with an acid.
[0054] The para-phenylenediamine derivative(s) of formula (I) are
used as oxidation bases in the composition intended for oxidation
dyeing or the ready-to-use oxidation dye composition in accordance
with the invention in concentrations ranging from 0.0001% to 20%,
preferably from 0.001% to 15% and even more particularly from 0.01%
to 10% by weight relative to the total weight of the
composition.
[0055] For the purposes of the present invention, the term
"alkanolamine" means any saturated or unsaturated, linear or
branched hydrocarbon compound containing from 2 to 100 carbon atoms
and comprising (i) at least one amine function optionally
substituted with one or two substituents that are preferably
C.sub.1-C.sub.4 alkyl or substituted C.sub.1-C.sub.4 alkyl such as,
for example, mono- or polyhydroxyalkyl, and (ii) at least one
hydroxyl function not borne by the amine function.
[0056] Preferably, the hydrocarbon chain is saturated.
[0057] Among the alkanolamines that may be used according to the
invention, mention may be made of monoethanolamine, diethanolamine,
triethanolamine, triisopropanolamine, 2-amino-2-methyl-1-propanol,
2-amino-2-methyl-1,3-propanediol, 2-amino-2-ethyl-1,3-propanediol,
2-amino-1-butanol, tris(hydroxy-methyl)aminomethane,
2-aminoethylethanolamine, 1-diethylamino-2,3-propanediol,
2-dimethylamino-2-methyl-1-propanol, dimethylethanolamine,
diethylethanolamine, ethylmonoethanolamine and
methylethanolamine.
[0058] Preferably, monoethanolamine is used.
[0059] The diaminoalkanes-used according to the invention are
preferably those of formula (II) below: 2
[0060] in which W is an alkylene residue optionally substituted
with a hydroxyl group or a C.sub.1-C.sub.4 alkyl radical; R.sub.5,
R.sub.6, R.sub.7 and R.sub.8, which may be identical or different,
represent a hydrogen atom or a C.sub.1-C.sub.4 alkyl or
C.sub.1-C.sub.4 hydroxyalkyl radical.
[0061] Preferably, W is a propylene residue.
[0062] Even more preferentially, the diaminoalkane is
diaminopropane.
[0063] Among all the alkaline agents that may be used according to
the invention, aqueous ammonia is preferably used.
[0064] The alkaline agent(s) is (are) present in the ready-to-use
oxidation dye composition or the composition intended for oxidation
dyeing according to the invention in concentrations ranging from
about 0.1% to about 20% by weight and preferably from about 0.5% to
about 10% by weight of active material relative to the total weight
of the composition intended for oxidation dyeing or the
ready-to-use oxidation dye composition.
[0065] The pH of the ready-to-use dyeing composition according to
the invention is preferably greater than 7 and even more
preferentially greater than 8.
[0066] The hydrogen peroxide present in the ready-to-use
composition according to the invention is used as an oxidizing
agent. It is present therein in a weight concentration of between
about 0.5% and 15% and preferably between about 1% and 10%, which
corresponds to an equivalent concentration of aqueous hydrogen
peroxide solution by volume of from about 1.6 to 50 volumes and
preferably from about 3.2 to 32 volumes.
[0067] The ready-to-use oxidation dye composition or the
composition intended for oxidation according to the invention
preferably contains at least one coupler.
[0068] Among these couplers, mention may be made especially of
meta-phenylenediamines, meta-aminophenols, meta-diphenols and
heterocyclic couplers such as, for example, indole derivatives,
indoline derivatives, benzimidazole derivatives, benzomorpholine
derivatives, sesamol derivatives, pyridine, pyrimdine and pyrazole
derivatives, and the addition salts thereof with an acid.
[0069] These couplers are more particularly chosen from
2-methyl-5-aminophenol,
5-N-(.beta.-hydroxyethyl)amino-2-methylphenol, 3-aminophenol,
1,3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene,
4-chloro-1,3-dihydroxybenzene,
2,4-diamino-1-(.beta.-hydroxyethyloxy)benz- ene,
2-amino-4-(.beta.-hydroxyethylamino)-1-methoxybenzene,
1,3-diaminobenzene, 1,3-bis(2,4-diaminophenoxy)propane, sesamol,
1-amino-2-methoxy-4,5-methylenedioxybenzene, .alpha.-naphthol,
2-methyl-1-naphthol, 6-hydroxyindole, 4-hydroxyindole,
4-hydroxy-N-methylindole, 6-hydroxyindoline,
2,6-dihydroxy-4-methylpyridi- ne, 1-H-3-methylpyrazol-5-one and
1-phenyl-3-methylpyrazol-5-one, and the addition salts thereof with
an acid.
[0070] The coupler(s) may be present in said composition according
to the invention in a concentration of between 0.0001% and 15% by
weight relative to the total weight of the composition.
[0071] The ready-to-use oxidation dye composition or the
composition intended for oxidation dyeing according to the
invention may also contain at least one additional oxidation base
other than the substituted para-phenylenediamine derivatives of
formula (I) and/or at least one direct dye.
[0072] Among the additional oxidation bases that may be used
according to the invention, mention may be made of
para-phenylenediamine, para-tolylenediamine,
2-hydroxyethyl-para-phenylenediamine,
1-N,N-bis(2-hydroxyethyl)-para-phenylenediamine, para-aminophenols
such as 3-methyl-4-aminophenol and 4-aminophenol,
ortho-phenylenediamines, ortho-aminophenols, double bases,
heterocyclic bases, for instance pyrimidines such as
2,4,5,6-tetraaminopyrimidine, or pyrazoles, such as
1-(2-hydroxyethyl)-4,5-diaminopyrazole.
[0073] The additional oxidation base(s) may be present in a
concentration of between 0.0001% and 15% by weight relative to the
total weight of said composition.
[0074] The medium that is suitable for dyeing (or the support) for
the dye composition according to the invention generally consists
of water or of a mixture of water and at least one organic solvent
to dissolve the compounds that would not be sufficiently
water-soluble. Examples of organic solvents that may be mentioned
include C.sub.1-C.sub.4 alkanols such as ethanol and isopropanol;
glycerol; glycols and glycol ethers, for instance 2-butoxyethanol,
propylene glycol, propylene glycol monomethyl ether, diethylene
glycol monomethyl ether and monoethyl ether, and also aromatic
alcohols, for instance benzyl alcohol or phenoxyethanol, similar
products and mixtures thereof.
[0075] The solvents may be present in proportions preferably of
between 1% and 40% by weight approximately relative to the total
weight of the dye composition, and even more preferentially between
5% and 30% by weight approximately.
[0076] The dye composition in accordance with the invention may
also contain various adjuvants conventionally used in compositions
for dyeing the hair, such as anionic, cationic, nonionic,
amphoteric or zwitterionic surfactants or mixtures thereof,
anionic, cationic, nonionic, amphoteric or zwitterionic polymers or
mixtures thereof, mineral or organic thickeners or thickening
polymers such as, for example, nonionic guar gums, antioxidants or
reducing agents, penetrating agents, sequestering agents,
fragrances, buffers, dispersants, conditioners such as, for
example, volatile or non-volatile silicones, which are modified or
unmodified, film-forming agents, ceramides, preserving agents and
opacifiers.
[0077] Preferably, the dye composition of the invention contains at
least one cationic polymer in a proportion of about from 0.05% to
10% by weight and at least one surfactant, preferably a nonionic
surfactant, in a proportion of from 0.1% to 20% by weight.
Preferably, it also contains at least one thickening polymer
preferably chosen from polymers comprising at least one hydrophilic
unit and at least one fatty chain in a proportion of about from
0.05% to 10% by weight.
[0078] Said composition may also contain reducing agents or
antioxidants. These may be chosen in particular from sodium
sulfite, thioglycolic acid, thiolactic acid, sodium bisulfite,
dehydroascorbic acid, hydroquinone, 2-methylhydroquinone,
tert-butylhydroquinone and homogentisic acid, and they are then
generally present in amounts ranging from about 0.05 to 1.5% by
weight, relative to the total weight of the composition.
[0079] Needless to say, a person skilled in the art will take care
to select this or these optional additional compound(s), such that
the advantageous properties intrinsically associated with the dye
composition in accordance with the invention are not, or are not
substantially, adversely affected by the envisaged addition(s).
[0080] The ready-to-use dye composition in accordance with the
invention may be in various forms, such as in the form of liquids,
powders, creams or gels, that may be pressurized, or in any other
form that is suitable for dyeing keratin fibers, and especially
human hair.
[0081] A subject of the invention is also a process for dyeing
keratin fibers, and in particular human keratin fibers such as the
hair, using the ready-to-use dye composition defined above.
[0082] According to this process, a dye composition containing, in
a medium that is suitable for dyeing, at least one substituted
para-phenylenediamine derivative of formula (I) is mixed, at the
time of use, with an oxidizing composition containing, in a medium
that is suitable for dyeing, at least hydrogen peroxide present in
an amount that is sufficient to develop a coloration, the alkaline
agent(s) defined above being present in one or both of the
compositions. The mixture obtained is then applied to the keratin
fibers and is left in place for 3 to 50 minutes approximately and
preferably 5 to 30 minutes approximately, after which the fibers
are rinsed, washed with shampoo, rinsed again and dried.
[0083] The dye composition before mixing with the hydrogen peroxide
may also be in various forms, such as in the form of liquid, cream
or gel, or in any other form that is suitable, after mixing, for
dyeing keratin fibers, and especially human hair.
[0084] Another subject of the invention is a multi-compartment
dyeing device or "kit" or any other multi-compartment packaging
system, at least one compartment of which contains a dye
composition containing at least one substituted
para-phenylenediamine derivative of formula (I) defined above and
another compartment of which contains an oxidizing composition
containing hydrogen peroxide, the alkaline agent(s) defined above
being present in one or both of the compositions. These devices may
be equipped with a means for applying the desired mixture to the
hair, such as the devices described in patent FR-2 586 913 in the
name of the Applicant.
[0085] The example that follows is intended to illustrate the
invention.
EXAMPLE 1
[0086] The dye composition below was prepared:
1 1-(4'-Amino-3'-methylphenyl)-4-hydroxy- 0.837 g
2-methylpyrrolidine dihydrochloride [substantituted
para-phenylenediamine derivative of formula (I) in accordance with
the invention] 2,4-Diamino-1-(.beta.-hydroxyethyloxy)benzene 0.723
g dihydrochloride Alkyl C.sub.8-C.sub.10 polyglucoside as an
aqueous 60% 3.24 g AM* solution, sold under the name Oramix CG 110
.RTM. by the company SEPPIC Ethanol 18 g Benzyl alcohol 1.8 g
Polyethylene glycol 400 2.7 g Pentasodium salt of
diethylenetriaminepenta- 0.43 g AM* acetic acid as an aqueous 40%
solution, sold under the name Dissoluine D-40 .RTM. by the company
Akzo Sodium metabisulphite 0.205 g Aqueous ammonia containing 20.5%
NH.sub.3.p 10 g Demineralized water qs 100 g AM* denotes Active
Material
[0087] At the time of use, the dye composition described above was
mixed weight for weight with a 20-volumes hydrogen peroxide
solution (6% by weight).
[0088] The mixture thus prepared was applied for 30 minutes to
locks of permanent-waved natural gray hair containing 90% white
hairs. The locks were then rinsed, washed with a standard shampoo,
rinsed again and then dried.
[0089] The hairs were dyed a bright blue shade.
* * * * *